DE4244539B4 - Duale Inhibitoren der No-Synthese und Cyclooxygenase, Verfahren zu ihrer Herstellung und therapeutische Präparate, die sie enthalten - Google Patents

Duale Inhibitoren der No-Synthese und Cyclooxygenase, Verfahren zu ihrer Herstellung und therapeutische Präparate, die sie enthalten Download PDF

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Publication number
DE4244539B4
DE4244539B4 DE4244539A DE4244539A DE4244539B4 DE 4244539 B4 DE4244539 B4 DE 4244539B4 DE 4244539 A DE4244539 A DE 4244539A DE 4244539 A DE4244539 A DE 4244539A DE 4244539 B4 DE4244539 B4 DE 4244539B4
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DE
Germany
Prior art keywords
compound
compounds
general formula
precursor
salt
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
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DE4244539A
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German (de)
English (en)
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DE4244539A1 (es
Inventor
Pierre Braquet
Colette Broquet
Serge Auvin
Piere-Etienne Chabrier De Lassauniere
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Ipsen Pharma SAS
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Societe de Conseils de Recherches et dApplications Scientifiques SCRAS SAS
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Publication of DE4244539A1 publication Critical patent/DE4244539A1/de
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Publication of DE4244539B4 publication Critical patent/DE4244539B4/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/02Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/03Monoamines
    • C07C211/04Mono-, di- or tri-methylamine
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/03Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
    • C07C65/05Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring o-Hydroxy carboxylic acids
    • C07C65/10Salicylic acid
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/06Antihyperlipidemics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/52Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C229/54Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C229/56Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position
    • C07C229/58Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position having the nitrogen atom of at least one of the amino groups further bound to a carbon atom of a six-membered aromatic ring, e.g. N-phenyl-anthranilic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/04Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C279/14Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/30Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to nitro or nitroso groups
    • C07C279/32N-nitroguanidines
    • C07C279/36Substituted N-nitroguanidines
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/44Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/30Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/12Acetic acid esters
    • C07C69/14Acetic acid esters of monohydroxylic compounds
    • C07C69/145Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
    • C07C69/157Acetic acid esters of monohydroxylic compounds of unsaturated alcohols containing six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/10Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/26Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
    • C07D209/281-(4-Chlorobenzoyl)-2-methyl-indolyl-3-acetic acid, substituted in position 5 by an oxygen or nitrogen atom; Esters thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
DE4244539A 1992-01-04 1992-12-30 Duale Inhibitoren der No-Synthese und Cyclooxygenase, Verfahren zu ihrer Herstellung und therapeutische Präparate, die sie enthalten Expired - Fee Related DE4244539B4 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB929200114A GB9200114D0 (en) 1992-01-04 1992-01-04 Dual inhibitors of no synthase and cyclooxygenase
GB9200114 1992-01-04

Publications (2)

Publication Number Publication Date
DE4244539A1 DE4244539A1 (es) 1993-07-08
DE4244539B4 true DE4244539B4 (de) 2006-10-26

Family

ID=10708115

Family Applications (1)

Application Number Title Priority Date Filing Date
DE4244539A Expired - Fee Related DE4244539B4 (de) 1992-01-04 1992-12-30 Duale Inhibitoren der No-Synthese und Cyclooxygenase, Verfahren zu ihrer Herstellung und therapeutische Präparate, die sie enthalten

Country Status (34)

Country Link
US (2) US5480999A (es)
JP (1) JP2984498B2 (es)
KR (1) KR100287539B1 (es)
AT (1) AT401054B (es)
AU (1) AU664399B2 (es)
BE (1) BE1006227A3 (es)
CA (1) CA2085555C (es)
CH (1) CH685629A5 (es)
DE (1) DE4244539B4 (es)
DK (1) DK157592A (es)
DZ (1) DZ1657A1 (es)
ES (1) ES2052452B1 (es)
FI (1) FI925883A (es)
FR (2) FR2685916B1 (es)
GB (2) GB9200114D0 (es)
GR (1) GR1001443B (es)
HK (1) HK22296A (es)
HU (1) HU220218B (es)
IE (1) IE71675B1 (es)
IT (1) IT1256761B (es)
LU (1) LU88208A1 (es)
MA (1) MA22753A1 (es)
MY (1) MY109846A (es)
NL (1) NL194889C (es)
NO (1) NO302943B1 (es)
NZ (1) NZ245499A (es)
OA (1) OA10050A (es)
PL (1) PL169432B1 (es)
PT (1) PT101165B (es)
RU (1) RU2104999C1 (es)
SE (1) SE511568C2 (es)
TN (1) TNSN93001A1 (es)
TW (1) TW267152B (es)
ZA (1) ZA9210080B (es)

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CA2188680A1 (en) * 1994-05-07 1996-01-25 James Edwin Macdonald Bicyclic amidine derivatives as inhibitors of nitric oxide synthetase
JPH10500129A (ja) 1994-05-11 1998-01-06 ジェス、オルセン 片頭痛の治療におけるnoスカベンジャー、阻害剤または拮抗剤の使用
CA2132690A1 (en) * 1994-09-22 1996-03-23 Dean Willis Control and modulation of inflammatory response in humans in need of such control and modulation
US6066333A (en) * 1994-09-22 2000-05-23 William Harvey Research Limited Pharmaceutical control of inflammation
FR2727111B1 (fr) * 1994-11-21 1997-01-17 Hoechst Lab Nouveaux analogues soufres d'aminoacides, leur procede de preparation et leurs applications comme medicaments
PT793646E (pt) 1994-11-23 2002-03-28 Biovitrum Ab Carboxilatos de aminoguanidina destinados ao tratamento de diabetes mellitus nao-insulinodependente
JPH08333258A (ja) 1994-12-14 1996-12-17 Japan Tobacco Inc チアジン又はチアゼピン誘導体及びそれら化合物を含有してなる一酸化窒素合成酵素阻害剤
ES2096524B1 (es) * 1994-12-22 1997-11-16 Sanchez Manuel Guerra Uso de la ng-monometil-l-arginina, para aumentar la capacidad de hacer ejercicio fisico.
FR2730930B1 (fr) * 1995-02-27 1997-04-04 Oreal Utilisation d'inhibiteurs de no-synthase pour diminuer l'effet irritant cutane de produits utilises dans le domaine cosmetique ou pharmaceutique
GB9504350D0 (en) * 1995-03-04 1995-04-26 Sod Conseils Rech Applic Arginine derivatives
US5703073A (en) * 1995-04-19 1997-12-30 Nitromed, Inc. Compositions and methods to prevent toxicity induced by nonsteroidal antiinflammatory drugs
GB9514518D0 (en) * 1995-07-15 1995-09-13 Sod Conseils Rech Applic Guanidine salt inhibitors of NO synthase and cyclooxygenase
CN1212620A (zh) * 1996-03-05 1999-03-31 儿童医院医疗中心 作为环氧酶抑制剂的巯基衍生物
WO1997044324A1 (en) 1996-05-21 1997-11-27 Pharmacia & Upjohn Company Aminoguanidine carboxylate lactams for the treatment of non-insulin-dependent diabetes mellitus
US5872145A (en) * 1996-08-16 1999-02-16 Pozen, Inc. Formulation of 5-HT agonist and NSAID for treatment of migraine
US8022095B2 (en) * 1996-08-16 2011-09-20 Pozen, Inc. Methods of treating headaches using 5-HT agonists in combination with long-acting NSAIDs
US6586458B1 (en) 1996-08-16 2003-07-01 Pozen Inc. Methods of treating headaches using 5-HT agonists in combination with long-acting NSAIDs
US5789395A (en) * 1996-08-30 1998-08-04 The Research Foundation Of State University Of New York Method of using tetracycline compounds for inhibition of endogenous nitric oxide production
IT1288123B1 (it) * 1996-09-04 1998-09-10 Nicox Sa Uso di nitroderivati per l'incontinenza urinaria
US6066092A (en) * 1997-11-06 2000-05-23 Cady; Roger K. Preemptive prophylaxis of migraine device and method
IT1301966B1 (it) 1998-07-30 2000-07-20 Zambon Spa Composizioni farmaceutiche ad attivita' analgesica
US6207700B1 (en) * 1999-01-07 2001-03-27 Vanderbilt University Amide derivatives for antiangiogenic and/or antitumorigenic use
US7345051B2 (en) * 2000-01-31 2008-03-18 Genaera Corporation Mucin synthesis inhibitors
US6737427B2 (en) * 2000-01-31 2004-05-18 Genaera Corporation Mucin synthesis inhibitors
JP2005539089A (ja) * 2002-07-03 2005-12-22 ニトロメッド インコーポレーティッド ニトロソ化非ステロイド性抗炎症化合物、組成物および使用方法
AU2003261281A1 (en) * 2002-07-29 2004-02-16 Nicox S.A. Cyclooxygenase- 2 selective inhibitors, compositions and methods of use
US7332183B2 (en) * 2002-12-26 2008-02-19 Pozen Inc. Multilayer dosage forms containing NSAIDs and triptans
WO2004110492A2 (en) * 2003-06-06 2004-12-23 Glaxo Group Limited Composition comprising triptans and nsaids
KR20060056444A (ko) * 2003-06-19 2006-05-24 제내라 코포레이션 뮤신 합성 억제제
EP1638612A4 (en) * 2003-06-25 2010-09-29 Univ Vanderbilt COX-2-MADE DISPLAY AGENTS
CN101031289A (zh) * 2004-04-26 2007-09-05 范德比尔特大学 作为具有降低胃肠毒性的治疗剂的吲哚乙酸和茚乙酸衍生物
AU2006204523A1 (en) * 2005-01-04 2006-07-13 Novartis Ag X-ray structure of human FPPS and use for selecting FPPS binding compounds
CA2657691A1 (en) * 2006-06-19 2007-12-27 Vanderbilt University Methods and compositions for diagnostic and therapeutic targeting of cox-2
EP3078374B1 (en) 2011-10-17 2019-06-19 Vanderbilt University Indomethacin analogs for the treatment of castrate-resistant prostate cancer
TWM469254U (zh) 2013-08-29 2014-01-01 J D Components Co Ltd 自行車之三件式豎管

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Publication number Priority date Publication date Assignee Title
DE4041283A1 (de) * 1989-12-22 1991-06-27 Scras Blockierungsmittel der edrf-wirkung oder -bildung fuer die behandlung von schockzustaenden
US5468476A (en) * 1994-03-16 1995-11-21 Ahluwalia; Gurpreet S. Reduction of hair growth

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FR2320759A1 (fr) * 1975-08-11 1977-03-11 Union Pharma Scient Appl Solution d'acide acetylsalicylique extemporanee injectable
IT1127274B (it) * 1979-12-04 1986-05-21 Selvi & C Spa Sali dell'acido 5-fluoro-2-metil-1-(p-(metilsulfinil)-benzilidene)-indene-3-acetico
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CA1213888A (en) * 1983-09-28 1986-11-12 Warner-Lambert Company L-arginine isoxicamate
US5081184A (en) * 1985-08-02 1992-01-14 General Electric Company Solvent-resistant, compatible blends of polyphenylene ethers and linear polyesters
JPS6393718A (ja) * 1986-10-07 1988-04-25 Green Cross Corp:The 注射剤
US5028627A (en) * 1989-09-13 1991-07-02 Cornell Research Foundation, Inc. Method of using arginine derivatives to inhibit systemic hypotension associated with nitric oxide production or endothelial derived relaxing factor
US5059712A (en) * 1989-09-13 1991-10-22 Cornell Research Foundation, Inc. Isolating aminoarginine and use to block nitric oxide formation in body
ATE128452T1 (de) * 1989-10-17 1995-10-15 Merck & Co Inc S(+)-ibuprofen-l-aminosäure und s(+)-ibuprofen-d- aminosäure als analgetika mit grösserem pharmakologischem potential.

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
DE4041283A1 (de) * 1989-12-22 1991-06-27 Scras Blockierungsmittel der edrf-wirkung oder -bildung fuer die behandlung von schockzustaenden
US5468476A (en) * 1994-03-16 1995-11-21 Ahluwalia; Gurpreet S. Reduction of hair growth

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Beilsteins Handbuch der Organischen Chemie. 4.Aufl., 4. Ergänzungswerk, Bd.4 S2652 u. 4.Aufl., 4. Ergänzungswerk, Bd.9 S.871
Beilsteins Handbuch der Organischen Chemie. 4.Aufl., 4. Ergänzungswerk, Bd.4 S2652 u. 4.Aufl.,4. Ergänzungswerk, Bd.9 S.871 *

Also Published As

Publication number Publication date
JPH05286916A (ja) 1993-11-02
KR930016389A (ko) 1993-08-26
PT101165B (pt) 1999-09-30
CH685629A5 (fr) 1995-08-31
BE1006227A3 (fr) 1994-06-14
FI925883A0 (fi) 1992-12-28
TW267152B (es) 1996-01-01
HK22296A (en) 1996-02-16
GB2263111A (en) 1993-07-14
DK157592A (da) 1993-07-05
DZ1657A1 (fr) 2002-02-17
SE9203825L (sv) 1993-07-05
NL194889C (nl) 2003-06-04
DE4244539A1 (es) 1993-07-08
HU9204173D0 (en) 1993-04-28
NO302943B1 (no) 1998-05-11
PL169432B1 (pl) 1996-07-31
ZA9210080B (en) 1993-08-02
IE922954A1 (en) 1993-07-14
TNSN93001A1 (fr) 1994-03-17
NL194889B (nl) 2003-02-03
SE9203825D0 (sv) 1992-12-18
AU664399B2 (en) 1995-11-16
SE511568C2 (sv) 1999-10-18
DK157592D0 (da) 1992-12-30
US5480999A (en) 1996-01-02
AT401054B (de) 1996-06-25
ATA256092A (de) 1995-10-15
US5360925A (en) 1994-11-01
CA2085555C (en) 2004-07-20
LU88208A1 (fr) 1993-04-15
PT101165A (pt) 1994-02-28
GB9227026D0 (en) 1993-02-17
NL9300001A (nl) 1993-08-02
PL297247A1 (en) 1993-09-06
AU3049892A (en) 1993-07-08
NO924835L (no) 1993-07-05
HUT64047A (en) 1993-11-29
ITMI922953A1 (it) 1994-06-23
IE71675B1 (en) 1997-02-26
MA22753A1 (fr) 1993-07-01
GR1001443B (el) 1993-12-30
GB9200114D0 (en) 1992-02-26
KR100287539B1 (ko) 2001-04-16
HU220218B (hu) 2001-11-28
FI925883A (fi) 1993-07-05
ES2052452A1 (es) 1994-07-01
CA2085555A1 (en) 1993-07-05
OA10050A (fr) 1996-10-14
NZ245499A (en) 1995-07-26
RU2104999C1 (ru) 1998-02-20
FR2685916A1 (fr) 1993-07-09
IT1256761B (it) 1995-12-15
FR2685869A1 (fr) 1993-07-09
GB2263111B (en) 1995-08-16
ES2052452B1 (es) 1995-02-01
MY109846A (en) 1997-08-30
JP2984498B2 (ja) 1999-11-29
NO924835D0 (no) 1992-12-14
FR2685869B1 (fr) 1995-06-09
FR2685916B1 (fr) 2001-09-28

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